When Solomon Schechter's landmark *Aspects of Rabbinic Theology* was reissued in 1961, Louis Finkelstein's introduction revealed both profound respect and critical engagement with his former mentor's theological vision. Through close reading of Finkelstein's introduction alongside Schechter's original work, and examination of their educational relationship at the Jewish Theological Seminary, a complex intellectual dialogue emerges between these two pillars of Conservative Judaism. While Finkelstein celebrates Schechter's revolutionary insight that Jewish theology must be experienced emotionally rather than merely understood intellectually, he identifies a crucial limitation: Schechter's failure to adequately connect Rabbinic theology with its juristic system. Finkelstein demonstrates this connection through his detailed analysis of a Talmudic case involving the tithing of spelt, illustrating how Rabbinic legal discourse serves to develop moral perceptivity. In doing so, Finkelstein successfully models the very experiential approach to Jewish theology that he attributes to Schechter, showing how theological understanding emerges through lived engagement with Jewish law and practice. This mentor-student dialogue illuminates the evolution of Conservative Jewish thought and the pedagogical dynamics of theological education.